The 2018 season has concluded, which means the offseason is now upon us. Over the next few months, there will inevitably be plenty of speculation about where free agents might end up signing and which players might be traded. Fans of teams hoping to contend are hopeful that their favourite team will acquire a star player or two who will lead them to the promised land and the World Series trophy in 2019.
Unfortunately, just like in every sport, there is a great deal of risk associated with any trade. In recent seasons, there have been countless trades that looked quite promising for both teams involved only for the trade to end up looking quite regrettable shortly thereafter. Every team makes mistakes and bad deals in professional sports - in fact, it happens quite often.
Every MLB team is guilty of having made a bad trade that they regret. If every team could go back in time and revert one poor trade they made, which one would they choose? That is precisely what we will be focusing on in this article, as we take a critical look at some of the bad trades that every MLB team has made in recent seasons.
30 Arizona Diamondbacks: Acquiring Shelby Miller
In December 2015, the Arizona Diamondbacks made a huge trade that will continue to haunt them for the foreseeable future. The Diamondbacks traded Dansby Swanson, Ender Inciarte, and Aaron Blair to the Atlanta Braves in exchange for starting pitcher Shelby Miller (and Gabe Speier as a throw-in). Since joining Arizona, Miller has struggled considerably and has spent more time on the Disabled List and in the minor leagues than he has helping the big league club. Conversely, Swanson and Inciarte have played big roles on the insurgent Atlanta Braves roster.
This is a trade that was widely panned at the time it was made, and it continues to look even more lopsided three years later.
29 Atlanta Braves: Trading Matt Kemp To The Dodgers
The Atlanta Braves entered the 2018 season expecting it to be a transition season, fielding a young roster filled with players they hoped would be part of their roster when they make the playoffs in the next few seasons. To make room for their younger players and clear salary, the Braves traded Matt Kemp to the Dodgers for Charlie Culberson, Adrian Gonzalez, Scott Kazmir, and Brandon McCarthy. The Braves released Gonzalez shortly thereafter.
The Braves, who surprised everyone when they won the N.L. East division, really could have used the productive Matt Kemp this season. Rather than the struggling veterans they received, Kemp would have provided a huge boost their offense.
28 Baltimore Orioles: Trading Kevin Gausman To The Braves
The Baltimore Orioles did the right thing when they sold off many of their major league roster pieces during the 2018 trade deadline. This ended up including starting pitcher Kevin Gausman, who was traded to the Atlanta Braves. Gausman is not an elite pitcher by any means, but he will be under control for a few more seasons and could still become a quality pitcher. The Orioles received a questionable return for Gausman, only getting a couple of middle of the road prospects - none of whom project to be everyday starters in the major leagues.
27 Boston Red Sox: Trading Travis Shaw To The Brewers
In December 2016, the Red Sox acquired Tyler Thornburg from the Milwaukee Brewers to try to upgrade their bullpen. The Red Sox hoped Thornburg would be able to depend the bullpen and serve as a set-up man for Craig Kimbrel. Unfortunately, Thornburg ended up spending quite a bit of time on the Disabled List. When he wasn't hurt, Thornburg struggled and ended up being left off the Red Sox 2018 playoff roster.
On the other hand, the Red Sox traded third base prospect Travis Shaw to the Brewers who has been fairly solid for the Brewers since the trade. Shaw has hit 30 home runs in both 2017 and 2018, making the trade a clear win for the Brewers.
26 Chicago Cubs: Acquiring Jose Quintana
In a rare Cubs-White Sox deal, the Cubs acquired starting pitcher Jose Quintana for a package of prospects which included top prospects Dylan Cease and Eloy Jimenez. The Cubs had hoped Quintana would emerge as a frontline starting pitcher, and that has so far failed to develop. Quintana has been decent enough since the trade, but has experienced his fair share of struggles. So far, the Cubs are likely regretting they traded Eloy Jimenez, who is arguably one of the best prospects in all of baseball, for Quintana.
25 Chicago White Sox: Acquiring Jeff Samardzija
The Chicago White Sox have done an excellent job at rebuilding, mostly through making smart trades that have helped them build one of the top farm systems in baseball. However, one trade that did not go as well as planned was when they acquired starting pitcher Jeff Samardzija in December 2014.
The White Sox were still trying to make the playoffs in 2015 and hoped Samardzija would help their cause, so they traded a couple of good prospects to Oakland. The 2015 season was one of Samardzija's worst, as he revealed he was tipping his pitches all season which led to a poor 4.96 ERA.
24 Cincinnati Reds: Acquiring Brandon Finnegan
At the 2015 MLB trade deadline, the Reds finally traded their ace starting pitcher Johnny Cueto. Unfortunately for the Reds, they couldn't capitalize on their biggest trade chip. The centerpiece of the deal was pitching prospect Brandon Finnegan, but the Reds also acquired minor leaguers John Lamb and Cody Reed. While Cueto went on to win a World Series with the Kansas City Royals,
Finnegan has struggled to live up to the expectations. While he got off to a decent start in 2017, his ERA started to climb in the second half of the season. In 2018, Finnegan only appeared in 5 games.
23 Cleveland Indians: Acquiring Josh Donaldson
The Cleveland Indians just barely managed to acquire Josh Donaldson by September 1, 2018. Essentially, Donaldson was hurt and barely able to play in minor league rehab games leading up to the trade. The Indians were aware of this, but agreed to the trade anyway. This led to other teams being annoyed at Cleveland, who they believe skirted the rule about revocable trade waiver transactions.
In the one month Donaldson was in Cleveland, Donaldson was hurt for about half of it and struggled to find any sort of consistency at the plate. For this barely minimal contribution, the Indians traded quality pitching prospect Julian Merryweather.
22 Colorado Rockies: Trading Corey Dickerson To The Rays
The Colorado Rockies have made several bold attempts to improve their bullpen in recent seasons. One of these moves included acquiring reliever Jake McGee from the Tampa Bay Rays for outfielder Corey Dickerson in January 2016. While 2016 was a rough year for Dickerson, he had a career season in 2017 for the Rays. In 2017, Dickerson had career bests in many offensive categories and was named to his first All-Star team.
Meanwhile, McGee has struggled to prevent runs - something especially concerning for their closer. In his three seasons with Colorado, McGee has a combined ERA of 4.90.
21 Detroit Tigers: Trading Justin Upton To The Angels
The August 2017 trade of Justin Upton was one that absolutely had to be done, as Upton was about to enter free agency. It was better the Tigers get something rather than simply letting Upton leave in free agency. However, the Tigers got only two barely notable prospects in the trade (Grayson Long and Elvin Rodriguez). It's hard to believe the Tigers could not get a better return for arguably one of the better outfielders in baseball. Upton re-signed with the Angels, and had another 30 home run season in 2018 while providing stellar defense in the outfield.
20 Houston Astros: Acquiring Roberto Osuna
Nobody really ends up benefitting from the Roberto Osuna situation, but the Astros arguably end up looking the worst. They admitted to knowing all the details of the situation involving Osuna, yet traded for him anyway. Even in the face of criticism from many fans, they acquired Osuna for Ken Giles, and two pitching prospects. Osuna's arrival did not sit well with many of the Astros players. Houston had a really tight-knit clubhouse and it looked as though Osuna's arrival interrupted that chemistry. This is probably a move GM Jeff Luhnow wishes he could take back.
19 Kansas City Royals: Acquiring Jorge Soler
Following the 2016 season, the Kansas City Royals traded one of their biggest trade chips in closer Wade Davis. The elite closer was sent to the Chicago Cubs, who had a dominant 2017 season. The Royals only landed outfielder Jorge Soler in the deal, which has not looked pretty for the Royals. Soler has experienced a great deal of inconsistency offensively and has battled a string of relentless DL stints since joining the Royals. He has improved somewhat while playing with the Royals' Triple-A affiliate, but one cannot help but wonder if the Royals could have gotten more for Wade Davis.
18 Los Angeles Angels: Trading C.J. Cron To The Rays
The L.A. Angels traded first baseman C.J. Cron the Tampa Bay Rays in February 2018 for a player to be named later. In 2018, Cron proceeded to have a breakout season hitting 30 home runs and 74 RBIs. He was a big reason why the Rays outperformed expectations in 2018, and at a very reasonable salary. In fairness, the Angels had Albert Pujols and Shohei Ohtani on the roster and had to make room at first base. With that being said, there is no doubt the Angels could have used that kind of production this past season.
17 Los Angeles Dodgers: Acquiring Manny Machado
The Los Angeles Dodgers have done everything they can to finally win the World Series with Clayton Kershaw on the roster. They fell just short in 2017, and they acquired Manny Machado at the 2018 trade deadline to hopefully give them that boost needed. The Dodgers gave up some excellent prospects to acquire Machado, who was mostly as advertised during the second half of the season.
Unfortunately, the Dodgers' bullpen was not upgraded and was one of the things that ended up costing them the World Series against Boston. Also not helping matters was Manny's lack of effort and hustle during the playoffs, which was widely criticized.
16 Miami Marlins: Trading Christian Yelich To The Brewers
The Miami Marlins made it very clear they were looking to dump as much payroll as possible, while boosting their farm system. The trade of Giancarlo Stanton was inevitable. Many were surprised the Marlins traded Christian Yelich, who was a top young talent on a team-friendly salary. Nevertheless, the Marlins traded him to the Brewers for a couple of prospects headlined by Lewis Brinson. In 2018, Yelich stepped it up and is a serious contender for the NL MVP Award while Brinson struggled for much of the season. The Marlins might be regretting having traded Yelich so soon, and for so little.
15 Milwaukee Brewers: Acquiring Jonathan Schoop
The Brewers surprised many people when they made the playoffs this year, largely because of their dynamic offence led by MVP candidate Christian Yelich. They had a solid offense, but decided to upgrade at second base and acquire Jonathan Schoop at the trade deadline. The deal was particularly puzzling because the Brewers had a bigger need in the starting rotation, where they could have used another quality starter or two.
The Brewers gave up some quality prospects for a player who did not fill a big need for the team. Making matters worse, Schoop struggled down the stretch and was not a major contributor during the team's playoff run.
14 Minnesota Twins: Trading Aaron Hicks To The Yankees
In November 2015, the Minnesota Twins dealt outfielder Aaron Hicks to the New York Yankees for catcher John Ryan Murphy. It wasn't a trade that most people thought much of at the time since both players were fairly unproven at the major league level. Since that time, Hicks has emerged as a quality outfielder with a good blend of speed, ability to hit for average, and power. He has provided the Yankees with quality depth in the outfield, which is something the Twins could have used in 2017 and 2018. Murphy, on the other hand, only spent a season with Minnesota - most of which was spent as a backup or in Triple-A.
13 New York Mets: Acquiring Jon Niese
In December 2015, the New York Mets traded Jon Niese to Pittsburgh for Neil Walker. A couple of months later, in July 2016, the Mets decided to re-acquire Niese. It is a mystery why the Mets decided to bring Niese back mere months after deciding he was expendable. The trade looks far worse when you consider that he only ended up appearing in only 1 game for the Mets since being re-acquired. Niese underwent season-ending surgery and hasn't been in the major leagues since. The Mets probably wish they never re-acquired Niese.
12 New York Yankees: Acquiring Sonny Gray
The Yankees have an uncanny ability to usually come out on the winning side of their trades. This was not the case when they traded for Sonny Gray at the 2017 trade deadline, sending three top prospects to the Oakland Athletics. Gray has been a complete flop for the Yankees, resulting in Gray being demoted to the bullpen and being left off their playoff roster.
The Yankees have all but admitted the Gray experiment was a flop and seem focused on trading him this offseason. While there are many teams who might be interested in Gray, the Yankees will still regret trading some of their top prospects to Oakland for him.
11 Oakland Athletics: Trading Josh Donaldson To The Blue Jays
Josh Donaldson emerged as one of the best players with the Oakland Athletics, before they stunningly traded him to the Toronto Blue Jays in the 2014 offseason. Many Athletics fans were annoyed the team traded the fan favourite and at the weak return for the elite slugger. Third baseman Brett Lawrie was the centerpiece of the trade for Oakland, but he only spent a single season with the Athletics and is now out of baseball. Donaldson, on the other hand, won the 2015 MVP and helped lead the Jays to back to back ALCS appearances in 2015 and 2016.
10 Philadelphia Phillies: Acquiring Asdrubal Cabrera
At the 2018 trade deadline, the Philadelphia Phillies made a series of moves hoping to catch up to the Atlanta Braves and win the division title. One of the notable acquisitions was infielder Asdrubal Cabrera, who was acquired from division-rival New York Mets. Cabrera did nothing to help the Phillies' cause, as he only hit .228 and 5 home runs in 49 games down the stretch.
Cabrera will be a free agent this offseason so he will probably not be a part of their future. Given that Cabrera will be playing for a different team next season, this mid-season acquisition is a disappointment for the Phillies.
9 Pittsburgh Pirates: Acquiring Chris Archer
The Pitsburgh Pirates front office make some strange decisions sometimes. In the offseason, they traded away ace starting pitcher Gerrit Cole only to end up acquiring another elite starter Chris Archer months later. The seemingly win-now move did not make much sense at the time, and looked even worse after the fact.
Archer sported an ERA north of 5.00 during the second half of 2018 and found himself on the Disabled List. Pittsburgh ought to work on rebuilding their farm system, not trading away prospects for a struggling Archer. The Pirates are probably hoping that Archer can go back to being a dominant frontline starter once again in 2019.
8 San Diego Padres: Acquiring Bryan Mitchell
Shortly after landing Giancarlo Stanton, the New York Yankees were looking to shed salary. Enter the San Diego Padres. They willingly took on Chase Headley and his salary in order to acquire pitcher Bryan Mitchell, whom they were especially interested in. Headley was released early in the season, but it remains to be seen why the Padres were so interested in Mitchell. He struggled considerably throughout 2018, and also spent some time on the Disabled List. While the Padres hoped Mitchell could become an effective starting pitcher, he ended up having to be a middle reliever in the bullpen.
7 San Francisco Giants: Acquiring Evan Longoria
During the 2017 offseason, the San Francisco Giants made a bold move and decided to go all in on contending in 2018. As part of that goal, they went out and acquired veteran third baseman Evan Longoria from Tampa Bay. That turned out to be a huge mistake as the team struggled throughout the season, and fell out of contention fairly quickly.
The Giants now face themselves with an aging roster who do not seem particularly likely to be contenders in 2019, and Madison Bumgarner only under contract for one more season. Bumgarner might be their one big trade chip as Longoria was merely league average in 2018 and is owed a lot of money for the next few seasons.
6 Seattle Mariners: Acquiring Zach Duke
The Seattle Mariners were surprisingly competitive in the tough AL West division, hanging around with the Astros and Angels longer than many had expected at the start of the season. However, their pitching staff has let the team down more often than not. In an attempt to bolster their bullpen, the Mariners acquired Zach Duke from the Minnesota Twins. While Duke was solid as a reliever for Minnesota, he posted an ERA well above 5.00 since the trade. The trade was not enough to secure Seattle a spot in the playoffs, and Duke will enter free agency this offseason.
5 St. Louis Cardinals: Acquiring Marcell Ozuna
The St. Louis Cardinals were close to acquiring Giancarlo Stanton, but he refused to play for St. Louis. Instead, the Cardinals shifted their attention to Marcell Ozuna as the man to provide some firepower in the middle of their lineup. To acquire Ozuna, the Cardinals traded some of their top prospects - including elite pitching prospect Sandy Alcantara. In 2018, Ozuna has been good but not great. He posted a decent enough batting average, but most of his hits were singles. That is not what the Cardinals were hoping they would get when they pulled off the huge trade for Ozuna!
4 Tampa Bay Rays: Acquiring Tommy Pham
The St. Louis Cardinals evidently did not foresee Tommy Pham as part of their future plans, even though he had a breakout season in 2017 and was a top prospect for the Cardinals. As a result, they traded him to the Tampa Bay Rays who were in search of any sort of offensive boost they could find. Pham had spent time in the minor leagues following a period of very poor performance at the plate in 2018. Since arriving in Tampa Bay, Pham struggled considerably and spent quite a bit of time on the Disabled List. Needless to say, this trade does not look good for the Rays so far.
3 Texas Rangers: Acquiring Willie Calhoun
This one is a bit tough, because the trade looked pretty solid for the Texas Rangers at the time it happened. The Rangers traded Yu Darvish to the L.A. Dodgers at the 2017 trade deadline, who ended playing a big role in propelling the Dodgers to the World Series (until Game 7 happened). Willie Calhoun was the centerpiece heading back to Texas, and he has not been faring so well thus far. He once looked near ready for the major leagues, but his struggles make it clear he will still require more time in Triple-A. While Calhoun might still develop as many had expected, this trade currently ranks as a regrettable one for Texas.
2 Toronto Blue Jays: Trading Noah Syndergaard To The Mets
The Blue Jays went all-in following the huge 2013 trade with the Miami Marlins, and set their sights on acquiring 2013 NL Cy Young winner R.A. Dickey. In order to acquire the knuckleballer, the Blue Jays had to give up top pitching prospect Noah Syndergaard. That ended up being a massive mistake as the veteran Dickey flamed out and often frustrated Jays fans with his highly unpredictable knuckleball during the four seasons he spent with the team. Syndergaard, on the other hand, emerged as one of baseball's best starting pitchers. Just imagine a Jays rotation with Syndergaard, Marcus Stroman, and Aaron Sanchez.
1 Washington Nationals: Acquiring Jonathan Papelbon
At the 2015 trade deadline, the rebuilding Philadelphia Phillies were shopping All-Star closer Jonathan Papelbon. The Washington Nationals thought they had won the sweepstakes when they acquired Papelbon - or so they thought. It quickly became apparent Papelbon was a problem in the clubhouse, getting into arguments with teammate Bryce Harper and intentionally throwing a pitch at Manny Machado's head during a game.
Papelbon was released a year later and has not played in the MLB ever since. Nick Pivetta, who the Phillies acquired in the trade, has been pretty decent in the starting rotation in 2018 and could be a big part of the team's future.